Reaction #2673

ord-9e556f57e168442bbbc24bcb8ff4afba

Reaction equation

COCCOCOc1c(C#N)ccc(C(Br)C(=O)O)c1OCOCCOC
product
COCCOCOc1c(C#N)ccc(C(Br)C(=O)O)c1OCOCCOC
[4-cyano-2,3-bis-[(2-methoxy-ethoxy)-methoxy]-phenyl]bromoacetic acid
[N-]=[N+]=C(c1ccccc1)c1ccccc1
diphenyl diazomethane
→
COCCOCOc1c(C#N)ccc(C(Br)C(=O)OC(c2ccccc2)c2ccccc2)c1OCOCCOC
Diphenylmethyl [4-cyano-2,3-bis-[(2-methoxy-ethoxy]-methoxy]phenyl]-bromoacetate

Reactants

COCCOCOc1c(C#N)ccc(C(Br)C(=O)O)c1OCOCCOC
product
COCCOCOc1c(C#N)ccc(C(Br)C(=O)O)c1OCOCCOC
[4-cyano-2,3-bis-[(2-methoxy-ethoxy)-methoxy]-phenyl]bromoacetic acid
[N-]=[N+]=C(c1ccccc1)c1ccccc1
diphenyl diazomethane

Reagents

None

Solvents

ClCCl
methylene chloride

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherEvaporation
  2. 2
    Otherto obtain 450 mg of the

Procedure

The product of Step A was dissolved in 10 ml of methylene chloride and 470 mg of diphenyl diazomethane were added. Evaporation was carried out followed by chromatography on silica (eluant: cyclohexane - ethyl acetate (2-1)) to obtain 450 mg of the desired, product.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05728828uspto-grants-1998_03